With warmer days and longer evenings, May is the perfect time to get outside and enjoy everything our vibrant community has to offer. From the creative energy of the Spring Art Walk to the lively atmosphere of Ales for Trails, there’s something for everyone this month. Whether you’re exploring local art, sipping craft brews for a good cause, or simply soaking up the sun. May is full of ways to connect, celebrate the season, and support local businesses. Don’t miss out—see you around town!
May 9th | Spring Art Walk
📍Last Chance Gulch from 4:00 – 8:00pm
Downtown Helena comes alive with local art, live music, food, and drinks. Stroll, sip, and soak up the creativity at the Spring Art Walk. It’s the perfect night to explore, connect, and support our community.
May 10th | Don’t Fence Me In Trail Run
📍Pioneer Park from 7:30am – 5:30 pm
It’s the 25th of the Twenty-five years ago, a race was born in the heart of Helena. What started as a grassroots effort to highlight the work of Prickly Pear Land Trust has grown into a beloved community tradition. The Don’t Fence Me In Trail Run is now a powerful symbol of conservation, connection, and pride in our wild spaces.All funds raised support parks, trails, and open lands throughout west-central Montana. After you cross the finish line, stick around for a big party in Pioneer Park — complete with food and beer, live music, dancing, balloon art, and yard games!
25K Race – $100 | 10:00 AM | SOLD OUT
12K Race – $60 | 10:30 AM
12K Walk – $60 | 10:45 AM
5K Race – $40 | 11:00 AM
5K Dog Walk – $40 | 11:00 AM
All courses now begin and end in Pioneer Park.
Kids 12 and under register for free. Registration closes the day at 10:00am. See you there!
https://runsignup.com/Race/Register/?raceId=20190
May 10th | Pots and Plants Market
📍Archie Bray Foundation (2915 Country Club Ave, Helena) from 10:00 am – 3:00 pm
The annual Pots and Plants Market is back. Explore a beautiful array of handcrafted pots, planters, and vases created by their talented artists—perfectly paired with lush plants generously donated by Home Depot and Lowe’s. As you shop, treat yourself to delicious bites from Flour’ish and a freshly brewed coffee from Montago Coffee. Plus, Good Omen Floral will be on-site with fresh-cut flowers to help you create the perfect gift.
May 16th | Ales for Trails
📍Pioneer Park from 3:30 – 5:30 pm (VIP event), 5:00 – 9:00 pm (Main Event)
In Helena Ales for Trails 14th year, this popular event supports the Helena Trail System and has raised over $223,000 for local trail projects. There will be exclusive small-batch and experimental beers, brewer meet-and-greets, and appetizers from Habana406. Be prepared to try beers from across states like Stevensville, Missoula, Darby and more.
VIP tickets are $50, include a custom tasting glass, one 6 oz pour token, and access to the main event. Tickets for the main event are $20 at local breweries, $25 online , or $35 at the gate (if available). Each ticket includes a glass and three 6oz pour tokens; additional tokens are $1 each.
You must be 21+ with valid ID to attend.
https://406tix.com/events/helena-ales-for-trails-2025-5-16-2025
May 17th | Holter Gala & Art Auction
📍Helena Civic Center from 5:30pm – dancing is done
The 2025 Holter Metamorphosis Gala & Art Auction is a wonderful way to support the Helena community through the arts. Guests are invited to wear their finest spring attire and enjoy an evening celebrating the city’s vibrant creative spirit. The event will feature wine and cocktails, locally sourced cuisine by The Union and Old Salt Co-op, interactive photo booths, and a live auction showcasing books transformed into remarkable works of art inspired by “Book Man” David Spencer.
Throughout the evening, guests can participate in an online silent auction (bring a charged phone), enjoy fun activities like the wine pull and Heads or Tails, and take part in Get Painted!, where local artists create wearable artwork on guests (tips appreciated). The auction program begins at 7:30 PM, with the silent auction closing at 8:15 PM, followed by dancing until 10 PM.
Individual tickets are $100, and tables of eight are available for $750. Sponsorship opportunities are also available. All proceeds support the Holter Museum of Art and its mission to enrich Helena through art and community engagement.
https://us.givergy.com/holterGALA2025/?controller=tickets
May 17th | Rodney Street Block Party
📍111 N. Rodney Street from 12:00 pm – 2:00 pm
This annual event brings the community together to promote mental health, substance use awareness, and overall wellness through food, resources, and connection. Local organizations that provide vital services in these areas are encouraged to participate. Space is limited, so early registration is strongly recommended. Interested organizations should complete the attached registration form to reserve a spot. Set-up will begin at 11:00am, and participants are reminded to bring their own tables and chairs.
